Thiourea, butyl- → HCID 22912058, compound

Participants

Reaction Steps

To a solution of 2-bromo-1-(4-fluorophenyl)-2- (4-methylsulfonylphenyl) ethanone (Example 26, Step 2) (0.384 g, 1.03 mmol) in ethanol (15 mL) in a 25 mL round bottom flask was added N-butylthiourea (0.144 g, 1.09 mmol). The solution was heated to reflux for 14 hours and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate, filtered and concentrated yielding 2-butylamino-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole (0.319 g, 77%) as an off-white fluffy solid: mp 134°-135° C., 1HNMR (DMSO d6) 7.94 (t, J=5.37 Hz, 1 H), 7.78 (d, J=8.79, 2 H), 7.45-7.36 (m, 4 H), 7.15 (t, J=8.79 Hz, 2H), 3.25 (q, J=5.37 Hz, 2 H), 3.18 (s, 3 H), 1.58-1.50 (m, 2 H), 1.41-1.32 (m, 2H), 0.90 (t, J=7.33 Hz, 3 H); MS (EI) m/z 404 (M+). HRMS Δ=1.1 mmu.

Provenance & Evidence